RU2013142992A - HIGH LATENCY HARDENERS FOR EPOXY RESIN - Google Patents

HIGH LATENCY HARDENERS FOR EPOXY RESIN Download PDF

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RU2013142992A
RU2013142992A RU2013142992/04A RU2013142992A RU2013142992A RU 2013142992 A RU2013142992 A RU 2013142992A RU 2013142992/04 A RU2013142992/04 A RU 2013142992/04A RU 2013142992 A RU2013142992 A RU 2013142992A RU 2013142992 A RU2013142992 A RU 2013142992A
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nhc
substituted
hardener
alkyl
dimethylurea
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RU2013142992/04A
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RU2586687C2 (en
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Сильвия ШТРОБЕЛЬ
Мартин ЭБНЕР
Ганс-Петер Криммер
Моника БРАНДЛЬ
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Альцхем Аг
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/44—Amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/44—Amides
    • C08G59/46—Amides together with other curing agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/21—Urea; Derivatives thereof, e.g. biuret
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Reinforced Plastic Materials (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1. Жидкий отвердитель для отверждения отверждаемых полимерных смол, в частности, эпоксидных смол, включающийa) цианамид;b) по меньшей мере, одно производное мочевины, описывающееся формулой (I) или формулой (II):где следующее далее относится к радикалам, в каждом случае одновременно или независимо друг от друга:R, R= одновременно или независимо друг от друга представляют собой водород, C1-C15 алкил, C3-C15 циклоалкил или совместно образуют кольцо С3-С10 алкилена;R= водород, C1-C15 алкил, C3-C15 циклоалкил, арил, арилалкил, -NHC(O)NRR-замещенный C1-C15 алкил, -NHC(O)NRR-замещенный С3-С15 циклоалкил, -NHC(O)NRR-замещенный арил или -NHC(O)NRR-замещенный арилалкил;R, R, R, R, R= одновременно или независимо друг от друга представляют собой водород, галоген, C1-C15 алкил, C3-C15 циклоалкил, арил, арилалкил, -CF, -NHC(O)NRR, -NHC(O)NRR-замещенный C1-C15 алкил, -NHC(O)NRR-замещенный арил или -NHC(O)NRR-замещенный арилалкил;и c) по меньшей мере, один стабилизатор, выбираемый из группы, включающей неорганические или органические кислоты.2. Жидкий отвердитель по п.1, характеризующийся тем, что отвердитель включает цианамид и, по меньшей мере, одно производное мочевины, описывающееся формулой (I) или формулой (II), при молярном соотношении цианамид: производное мочевины или смесь производных мочевины в диапазоне от 1:1 до 4:1.3. Жидкий отвердитель по п.1, характеризующийся тем, что отвердитель помимо цианамида, по меньшей мере, одного производного мочевины и стабилизатора не включает каких-либо растворителя или солюбилизатора или является свободным от растворителей или солюбилизаторов.4. Жидкий отвердитель по п.1, характеризующийся тем, что отвердитель включает, по меньшей мере, два различных производных мочевины.1. A liquid hardener for the curing of curable polymer resins, in particular epoxy resins, comprising a) cyanamide; b) at least one urea derivative described by formula (I) or formula (II): wherein the following refers to radicals, in each case simultaneously or independently from each other: R, R = simultaneously or independently from each other represent hydrogen, C1-C15 alkyl, C3-C15 cycloalkyl or together form a C3-C10 alkylene ring; R = hydrogen, C1-C15 alkyl, C3 —C15 cycloalkyl, aryl, arylalkyl, —NHC (O) NRR substituted C1-C15 alkyl, —NHC (O) NRR substituted C3-C15 cycloalkyl, -NHC (O) NRR-substituted aryl or -NHC (O) NRR-substituted arylalkyl; R, R, R, R, R = simultaneously or independently from each other are hydrogen, halogen, C1- C15 alkyl, C3-C15 cycloalkyl, aryl, arylalkyl, -CF, -NHC (O) NRR, -NHC (O) NRR-substituted C1-C15 alkyl, -NHC (O) NRR-substituted aryl or -NHC (O) NRR-substituted arylalkyl; and c) at least one stabilizer selected from the group consisting of inorganic or organic acids. 2. The liquid hardener according to claim 1, characterized in that the hardener comprises cyanamide and at least one urea derivative described by formula (I) or formula (II), in a molar ratio of cyanamide: urea derivative or a mixture of urea derivatives in the range of 1 : 1 to 4: 1.3. The liquid hardener according to claim 1, characterized in that the hardener, in addition to the cyanamide of at least one urea derivative and stabilizer, does not include any solvent or solubilizer or is free of solvents or solubilizers. The liquid hardener according to claim 1, characterized in that the hardener comprises at least two different urea derivatives.

Claims (12)

1. Жидкий отвердитель для отверждения отверждаемых полимерных смол, в частности, эпоксидных смол, включающий1. A liquid hardener for curing curable polymer resins, in particular epoxies, including a) цианамид;a) cyanamide; b) по меньшей мере, одно производное мочевины, описывающееся формулой (I) или формулой (II):b) at least one urea derivative described by formula (I) or formula (II):
Figure 00000001
Figure 00000002
Figure 00000001
Figure 00000002
 где следующее далее относится к радикалам, в каждом случае одновременно или независимо друг от друга:where the following further relates to radicals, in each case simultaneously or independently of one another: R1, R2 = одновременно или независимо друг от друга представляют собой водород, C1-C15 алкил, C3-C15 циклоалкил или совместно образуют кольцо С3-С10 алкилена;R 1 , R 2 = simultaneously or independently from each other represent hydrogen, C1-C15 alkyl, C3-C15 cycloalkyl or together form a ring C3-C10 alkylene; R3 = водород, C1-C15 алкил, C3-C15 циклоалкил, арил, арилалкил, -NHC(O)NR1R2-замещенный C1-C15 алкил, -NHC(O)NR1R2-замещенный С3-С15 циклоалкил, -NHC(O)NR1R2-замещенный арил или -NHC(O)NR1R2-замещенный арилалкил;R 3 = hydrogen, C1-C15 alkyl, C3-C15 cycloalkyl, aryl, arylalkyl, -NHC (O) NR 1 R 2 -substituted C1-C15 alkyl, -NHC (O) NR 1 R 2 -substituted C3-C15 cycloalkyl , -NHC (O) NR 1 R 2 -substituted aryl or -NHC (O) NR 1 R 2 -substituted arylalkyl; R4, R5, R6, R7, R8 = одновременно или независимо друг от друга представляют собой водород, галоген, C1-C15 алкил, C3-C15 циклоалкил, арил, арилалкил, -CF3, -NHC(O)NR1R2, -NHC(O)NR1R2-замещенный C1-C15 алкил, -NHC(O)NR1R2-замещенный арил или -NHC(O)NR1R2-замещенный арилалкил;R 4 , R 5 , R 6 , R 7 , R 8 = simultaneously or independently from each other are hydrogen, halogen, C1-C15 alkyl, C3-C15 cycloalkyl, aryl, arylalkyl, -CF 3 , -NHC (O) NR 1 R 2 , —NHC (O) NR 1 R 2 —substituted C1-C15 alkyl, —NHC (O) NR 1 R 2 —substituted aryl, or —NHC (O) NR 1 R 2 —substituted arylalkyl; и c) по меньшей мере, один стабилизатор, выбираемый из группы, включающей неорганические или органические кислоты.and c) at least one stabilizer selected from the group consisting of inorganic or organic acids. 2. Жидкий отвердитель по п.1, характеризующийся тем, что отвердитель включает цианамид и, по меньшей мере, одно производное мочевины, описывающееся формулой (I) или формулой (II), при молярном соотношении цианамид: производное мочевины или смесь производных мочевины в диапазоне от 1:1 до 4:1.2. The liquid hardener according to claim 1, characterized in that the hardener comprises cyanamide and at least one urea derivative described by formula (I) or formula (II) with a molar ratio of cyanamide: urea derivative or a mixture of urea derivatives in the range from 1: 1 to 4: 1. 3. Жидкий отвердитель по п.1, характеризующийся тем, что отвердитель помимо цианамида, по меньшей мере, одного производного мочевины и стабилизатора не включает каких-либо растворителя или солюбилизатора или является свободным от растворителей или солюбилизаторов.3. The liquid hardener according to claim 1, characterized in that the hardener, in addition to cyanamide, at least one urea derivative and stabilizer, does not include any solvent or solubilizer or is free of solvents or solubilizers. 4. Жидкий отвердитель по п.1, характеризующийся тем, что отвердитель включает, по меньшей мере, два различных производных мочевины.4. The liquid hardener according to claim 1, characterized in that the hardener includes at least two different derivatives of urea. 5. Жидкий отвердитель по п.1, характеризующийся тем, что отвердитель включает производное мочевины, описывающееся формулой (I), где следующее далее относится к радикалам, в каждом случае одновременно или независимо друг от друга:5. The liquid hardener according to claim 1, characterized in that the hardener comprises a urea derivative described by formula (I), where the following further relates to radicals, in each case, simultaneously or independently from each other: R1 и R2 = водород, C1-C15 алкил;R 1 and R 2 = hydrogen, C1-C15 alkyl; R3 = водород, C1-C15 алкил, C3-C15 циклоалкил, -NHC(O)NR1R2-замещенный C1-C15 алкил, -NHC(O)NR1R2-замещенный C3-C15 циклоалкил или -NHC(O)NR1R2-замещенный арил.R 3 = hydrogen, C1-C15 alkyl, C3-C15 cycloalkyl, -NHC (O) NR 1 R 2 -substituted C1-C15 alkyl, -NHC (O) NR 1 R 2 -substituted C3-C15 cycloalkyl or -NHC ( O) NR 1 R 2 -substituted aryl. 6. Жидкий отвердитель по п.1, характеризующийся тем, что отвердитель содержит a) цианамид, b) производное мочевины, выбираемое из группы, включающей мочевину, 1,1-диметилмочевину, 3-(3-хлор-4-метилфенил)-1,1-диметилмочевину, 3-(п-хлорфенил)-1,1-диметилмочевину, 3-фенил-1,1-диметилмочевину, 3-(3,4-дихлорфенил)-1,1-диметилмочевину, 1,1′-(метиленди-п-фенилен)бис(3,3-диметилмочевину), 3-(3-трифторметилфенил)-1,1 -диметилмочевину, 1,1′-(2-метил-м-фенилен)бис(3,3-диметилмочевину) и/или 1,1′-(4-метил-м-фенилен)бис(3,3-диметилмочевину), и c) по меньшей мере, один стабилизатор, выбираемый из группы, включающей неорганические или органические кислоты.6. The liquid hardener according to claim 1, characterized in that the hardener contains a) cyanamide, b) a urea derivative selected from the group consisting of urea, 1,1-dimethylurea, 3- (3-chloro-4-methylphenyl) -1 , 1-dimethylurea, 3- (p-chlorophenyl) -1,1-dimethylurea, 3-phenyl-1,1-dimethylurea, 3- (3,4-dichlorophenyl) -1,1-dimethylurea, 1,1′- (methylenedi-p-phenylene) bis (3,3-dimethylurea), 3- (3-trifluoromethylphenyl) -1,1-dimethylurea, 1,1 ′ - (2-methyl-m-phenylene) bis (3,3- dimethylurea) and / or 1,1 ′ - (4-methyl-m-phenylene) bis (3,3-dimethylurea), and c) at least one stabilizer, select th from the group consisting of inorganic or organic acids. 7. Жидкий отвердитель, по меньшей мере, по одному из предшествующих пунктов, характеризующийся тем, что в качестве неорганической или органической кислоты используют кислоту, выбираемую из группы, включающей салициловую кислоту, фталевую кислоту, толуолсульфоновую кислоту, серную кислоту, фосфорную кислоту или их ангидриды или их смеси.7. A liquid hardener, according to at least one of the preceding claims, characterized in that an inorganic or organic acid is an acid selected from the group consisting of salicylic acid, phthalic acid, toluenesulfonic acid, sulfuric acid, phosphoric acid or their anhydrides or mixtures thereof. 8. Композиция эпоксидной смолы, включающая8. The composition of the epoxy resin, including a) по меньшей мере, одну отверждаемую эпоксидную смолу иa) at least one curable epoxy resin and b) по меньшей мере, один жидкий отвердитель, по меньшей мере, по одному из предшествующих пп.1-7.b) at least one liquid hardener, at least one of the preceding claims 1 to 7. 9. Композиция полиуретановой смолы, включающая9. The composition of the polyurethane resin, including a) по меньшей мере, одну отверждаемую полиуретановую смолу иa) at least one curable polyurethane resin and b) по меньшей мере, один жидкий отвердитель, по меньшей мере, по одному из предшествующих пп.1-7.b) at least one liquid hardener, at least one of the preceding claims 1 to 7. 10. Композитный материал, включающий10. Composite material, including a) материал носителя, в частности, волокнистый материал,a) carrier material, in particular fibrous material, b) по меньшей мере, одну отверждаемую эпоксидную смолу и/или отверждаемую полиуретановую смолу иb) at least one curable epoxy resin and / or a curable polyurethane resin and c) по меньшей мере, один жидкий отвердитель, по меньшей мере, по одному из предшествующих пп.1-7.c) at least one liquid hardener, at least one of the preceding claims 1 to 7. 11. Применение жидкого отвердителя, по меньшей мере, по одному из предшествующих пп.1-7 для отверждения композиций, включающих, по меньшей мере, одну отверждаемую эпоксидную смолу и/или отверждаемую полиуретановую смолу.11. The use of a liquid hardener in at least one of the preceding claims 1 to 7 for curing compositions comprising at least one curable epoxy resin and / or a curable polyurethane resin. 12. Применение жидкого отвердителя, по меньшей мере, по одному из предшествующих пп.1-7 для отверждения импрегнированных волокнистых материалов или импрегнированных тканых материалов, вязаных материалов или оплеток. 12. The use of a liquid hardener in at least one of the preceding claims 1 to 7 for curing impregnated fibrous materials or impregnated woven materials, knitted materials or braids.
RU2013142992/04A 2011-02-23 2012-02-23 High latency curing agents for epoxy resins RU2586687C2 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE201110012079 DE102011012079A1 (en) 2011-02-23 2011-02-23 Liquid hardener useful e.g. for hardening of hardenable polymer resins, preferably epoxy resins, comprises cyanamide and at least one urea derivative
DE102011012079.3 2011-02-23
DE102012000674 2012-01-17
DE102012000674.8 2012-01-17
PCT/EP2012/053091 WO2012113878A1 (en) 2011-02-23 2012-02-23 High-latency hardeners for epoxy resins

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